Hydrochloric Acid → 1-[3-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-prop-2-ynyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid

HRID 1253772Notes

Reaction equation

HRID 1253772 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:15][C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[O:28][N:27]=[C:26]([CH3:29])[C:25]=3[NH:30][C:31]([O:33][CH:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])[CH3:35])=[O:32])=[CH:20][CH:19]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.CO.[OH-].[Li+].Cl>O>[Cl:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[CH:34]([O:33][C:31]([NH:30][C:25]1[C:26]([CH3:29])=[N:27][O:28][C:24]=1[C:21]1[CH:20]=[CH:19][C:18]([C:17]#[C:16][CH2:15][N:9]2[C:10]([C:11]([F:14])([F:13])[F:12])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)=[CH:23][CH:22]=1)=[O:32])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 685296471-[3-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-prop-2-ynyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 462398851-[3-(4-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-prop-2-ynyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-[3-(4-{4-[1-(2-chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-prop-2-ynyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.155 g, 0.26 mmol) in 2:1 MeOH:H2O (3 mL) was added lithium hydroxide (0.033 g, 0.79 mmol), and the reaction was stirred overnight at room temperature. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc, and the combined organic layers were dried, filtered, and concentrated. The residue was purified by preparative HPLC to give the title compound. Mass spec. data (M+H)=573.

Workup

  1. extractionextracted with EtOAc
  2. customthe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d2eb65d0c7e34f5b98fb68ed7de6226b
Source dataset
uspto-grants-2013_06
Patent number
US08455499B2

Reaction notes

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